Ethyl Acetate → 2-Hydroxymethyl-5-pentadecylphenol

HRID 2309846Notes

Reaction equation

HRID 2309846 reaction equation
[CH2:1]([C:16]1[CH:17]=[C:18]([OH:25])[C:19](=[CH:23][CH:24]=1)[C:20](O)=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C>O1CCCC1>[CH2:1]([C:16]1[CH:17]=[C:18]([OH:25])[C:19](=[CH:23][CH:24]=1)[CH2:20][OH:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 37931474-Pentadecylsalicylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 198183062-Hydroxymethyl-5-pentadecylphenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

4-Pentadecylsalicylic acid (5.3 g) in dry tetrahydrofuran (60 cm3) is slowly added to stirred lithium aluminium hydride (2.5 g) in dry tetrahydrofuran (25 cm3) and the mixture then stirred and refluxed for five hours to complete the reduction. Work-up by recovery of the tetrahydrofuran, addition of a little ethyl acetate to the cooled residual material, followed by acidifiction and ethereal extraction yields the crude product which is crystallised from light petroleum (40°-60°) to give 4-pentadecylsalicyl alcohol as pale cream prisms, m.p. 94°-95°, (4.05 g).

Workup

  1. temperaturerefluxed for five hours
  2. extractionfollowed by acidifiction and ethereal extraction
  3. customyields the crude product which
  4. customis crystallised from light petroleum (40°-60°)

Sources & evidence

ORD record
ord-28ed5ca776a74ee4921781e221413cb4
Source dataset
uspto-grants-1987_09
Patent number
US04697038

Reaction notes

Loading…