HCID 19995396, compound → HCID 19995384, compound

HRID 979254Notes

Reaction equation

HRID 979254 reaction equation
C([O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]3[CH:24]=[CH:23][C:22]4[C:21]([CH3:26])([CH3:25])[CH2:20][CH2:19][C:18]([CH3:28])([CH3:27])[C:17]=4[CH:16]=3)[CH:13]=2)[CH:8]=[C:7]([C:29]([O:31]C)=[O:30])[CH:6]=1)(=O)C>O>[OH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]3[CH:24]=[CH:23][C:22]4[C:21]([CH3:25])([CH3:26])[CH2:20][CH2:19][C:18]([CH3:27])([CH3:28])[C:17]=4[CH:16]=3)[CH:13]=2)[CH:8]=[C:7]([C:29]([OH:31])=[O:30])[CH:6]=1

Participants

3

Reactant 1

HCID 19995396HCID 19995396, compound

Product 1

HCID 19995384HCID 19995384, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.7 g (3.95 mmoles) of ester obtained in Example 1 are added to a mixture of 100 ml of methanolic soda (2M) and 50 ml of water. The mixture is heated for 4 hours, evaporated dry, and, after 100 ml of water are added, extracted with ether (300 ml). The aqueous phase of the product is recuperated, brought to pH 1 with concentrated hydrochloric acid. After extraction of the precipitate with ether (300 ml), it is washed in water until neutral, then dried and evaporated. The solid obtained is recrystallized in acetonitrile. Thus is obtained 1.3 g (88%) of 4-hydroxy-6-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-2-naphthoic acid which melts at 299° C.

Workup

  1. temperatureThe mixture is heated for 4 hours
  2. customevaporated
  3. customdry
  4. additionafter 100 ml of water are added
  5. extractionextracted with ether (300 ml)
  6. extractionAfter extraction of the precipitate with ether (300 ml), it
  7. washis washed in water until neutral,
  8. customthen dried
  9. customevaporated
  10. customThe solid obtained
  11. customis recrystallized in acetonitrile

Sources & evidence

ORD record
ord-978055d02760405297eb9749f5931bc7
Source dataset
uspto-grants-1987_05
Patent number
US04666941

Reaction notes

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