C[O:2][C:3]1[CH:4]=[C:5]([C:9]2([CH:15]3C(=O)OC(C)(C)[O:17][C:16]3=[O:24])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.C1(OC)C(C(O)=O)=CC=CC=1.[OH-].[Na+].C(S)CCCCCCCCCCC>CN1CCCC1=O.O>[OH:2][C:3]1[CH:4]=[C:5]([C:9]2([CH2:15][C:16]([OH:24])=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1
5-(1-(3-Methoxyphenyl)cyclohexyl)-2,2-dimethyl-1,3-dioxane-4,6-dione (105.B) (985 mg, 2.96 mmol) was dissolved in N-methylpyrrolidinone (6.0 mL) and water (53.4 μL, 2.96 mmol) was added. The solution was heated at 120° C. for three hours and LCMS indicated conversion to the anisole carboxylic acid intermediate. The reaction was cooled and NaOH (530 mg, 13.3 mmol) and commercially available dodecane-1-thiol (2.47 mL, 10.4 mmol) were added and the mixture was reheated to 120° C. and stirred for 2.5 days. The reaction was cooled and then diluted with water (75 mL). The mixture was extracted with ether (2×75 mL). The aqueous layer was then acidified with hydrochloric acid and extracted with EtOAc (3×75 mL). The combined EtOAc layers were washed with water (2×100 mL) and brine (1×75 mL) and dried over magnesium sulfate. The filtrate was concentrated to give 2-(1-(3-hydroxyphenyl)cyclohexyl)acetic acid 105.C (1.01 g, 145% yield) with acceptable purity (contains residual N-methylpyrrolidone) to take to the next reaction. MS ESI (neg.) m/e: 233.1 (M−H)−.
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