Methyl 3-methyl-6-(phenylthio)-benzoate → HCID 12539099, compound

HRID 435664Notes

Reaction equation

HRID 435664 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9]([S:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:10][CH:11]=1)[C:5](OC)=[O:6]>O1CCCC1.C1C=CC=CC=1.Cl>[CH3:1][C:2]1[CH:3]=[C:4]([C:9]([S:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:10][CH:11]=1)[CH2:5][OH:6]

Participants

5

Reactant 1

HCID 21481132Methyl 3-methyl-6-(phenylthio)-benzoate

Product 1

HCID 12539099HCID 12539099, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolvent2×HCID 313Hydrochloric AcidSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

322.5 g of methyl 3-methyl-6-(phenylthio)-benzoate in 3 litres of absolute tetrahydrofuran are treated dropwise over a period of 30 minutes under argon and under reflux with 420 ml of a 70% sodium-dihydro-bis(2-methoxyethoxy)-aluminate solution in benzene and the mixture is boiled for a further 3 hours under reflux. Then the mixture is cooled to ca 4° C, diluted with 1 litre of benzene, hydrolysed with 700 ml of 2-N hydrochloric acid, then poured on to ice-water and treated with a further 400 ml of concentrated hydrochloric acid in order to obtain a clear solution. The organic phase is washed with water, dried over sodium sulphate, filtered and evaporated. There is obtained 3-methyl-6-(phenylthio)-benzyl alcohol as a red-brown oil.

Workup

  1. temperatureunder reflux
  2. temperatureThen the mixture is cooled to ca 4° C
  3. customto obtain a clear solution
  4. washThe organic phase is washed with water
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-090467a5b32441e2a20ef71aee92d5fe
Source dataset
uspto-grants-1977_02
Patent number
US04006144

Reaction notes

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